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Androstane compound and its preparation method and application

The technology of a compound, androstanedione, is applied in a class of androstanoids and its preparation and use, which can solve the problems of high market costs and achieve low cost effects

Active Publication Date: 2010-05-12
SHANGHAI INST OF PHARMA IND CO LTD +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Hydrocortisone (IV) market cost in this method is higher, and used a large amount of benzene in the reaction

Method used

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  • Androstane compound and its preparation method and application
  • Androstane compound and its preparation method and application
  • Androstane compound and its preparation method and application

Examples

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preparation example Construction

[0024] The preparation method of the above-mentioned compound of formula (I) is prepared by sulfonylation of compound 11α-hydroxy-4-ene-3,17-androstandione of formula (II); the reaction formula is as follows.

[0025]

[0026] The above preparation method is to dissolve 11α-hydroxy-4-ene-3,17-androstadione (II) in a dry organic solvent, add a deacidification agent, add a sulfonylation reagent at a low temperature, and react for 5 to 40 minutes. hour, then the reaction solution is poured into a large amount of water to separate out solids, which is the compound of formula (I), i.e. androsteroids, also known as 11α-hydroxysulfonate; wherein the reaction temperature is -20~50°C, and the pH of the reaction solution =8.0-11.0; the molar ratio of 11α-hydroxy-4-ene-3,17-androstadione (II):sulfonylation reagent is 1:1.0~1:4.0.

[0027] In the above preparation method, the selected sulfonylation reagent is lower alkylsulfonyl chloride, aromatic sulfonyl chloride or the corresponding...

Embodiment 1

[0040] Preparation of 11α-p-toluenesulfonyloxy-4-ene-3,17-androstandione (Ia)

[0041] Dissolve 435.0 g (1.44 mol) of 11α-hydroxy-4-ene-3,17-androstadione (II) in 3 L of dry pyridine, and add 420.0 g (2.20 mol) of p-toluenesulfonyl chloride at -20°C , stirred for 3 hours, warmed up to room temperature and reacted for 12 hours, then poured the reaction solution into 10L of ice water, precipitated solid, filtered and dried to obtain 622.0g off-white solid, the compound is 11α-p-toluenesulfonyloxy- 4-ene-3,17-androstadione (Ia), yield 94.7%. The melting point is 138-140°C.

Embodiment 2

[0043] Preparation of 11α-p-toluenesulfonyloxy-4-ene-3,17-androstandione (Ia)

[0044] Dissolve 43.5 g (0.15 mol) of 11α-hydroxy-4-ene-3,17-androstadione (II) in 300 ml of dry triethylamine, and add 42.0 g (0.22 mol), stirred for 5 hours, warmed up to room temperature and reacted for 24 hours, then poured the reaction solution into 1L of ice water, precipitated solid, filtered, and dried to obtain 61.0g off-white solid, the compound is 11α-p-toluenesulfonyloxy The yield of 4-en-3,17-androstanedione (Ia) was 87.5%. The melting point is 138-140°C.

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Abstract

The invention provides a compound that is demonstrated in general formula I. The R in formula I can be low- grade alkyl sulfonyl, aryl sulfonyl chloride or relevant halosulfonyl. Said compound is prepared by taking 11 alpha- hydroxy- 4- ene- 3, 17- androsterone and through sulfoacylation process. The invention aslo discloses the application of said compound in preparation of medical intermediate 4, 9(11) - diene- 3, 17- androsterone. The productivity for 4, 9(11) - diene- 3, 17- androsterone is above 92%, and the cost is low. The invention is suitable for large- scale production.

Description

technical field [0001] The present invention relates to a class of compounds and the preparation method of this class of compounds and the purposes of this class of compounds in the preparation of medicines, specifically a class of androsteroid compounds and the preparation method of this class of androsteroid compounds and the use of this class of androsteroid compounds in Application of the pharmaceutical intermediate 4,9(11)-diene-3,17-androstadione in the preparation of the selective aldosterone antagonist eplerenone. Background technique [0002] Androsteroids are a class of steroidal compounds, and their steroidal compounds include cyclopentane[a]hydrophenanthrene skeletons, or ring structures derived from it: androsteroids belong to the orthodox series containing carbon, hydrogen, halogen or oxygen Steroids, unsubstituted by a carbon atom at position 17β. [0003] 4,9(11)-diene-3,17-androstadione (III) in androsteroids is an important pharmaceutical intermediate for ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07J31/00C07J1/00
Inventor 王显连钟静芬时惠麟
Owner SHANGHAI INST OF PHARMA IND CO LTD